The Ultimate Italy Road Trip: 14 Days Through Florence, Venice & Tuscany

Are you going on a road trip in Italy? Discover Florence, Venice, Tuscany, Pisa & Cinque Terre on our 14-day road trip starting and ending in Milan.

A road trip in Italy, packed with some of the country’s most stunning landscapes and iconic cities—sounds good, right? Olive groves, charming villages, gelato, canals, vineyards, Renaissance palaces, rolling hills, and pizza—this trip had it all! Here’s my suggested two-week road trip in northern Italy, featuring all my favorite spots north of Rome.

We spent 11 days driving through northern Italy, but if I could do it again, I’d add three extra days—one more in Florence, another in Venice, and a day at Lake Como—making it a 14-day itinerary. Even though we traveled in the low season, traffic and crowds made it tricky to see everything we wanted. It’s better to have a slightly more relaxed schedule and take the time to actually enjoy the experience—after all, you’re in Italy!

Want to learn more about what it’s really like to drive in Italy? Check out my full guide here! How to Drive in Italy: Tips for a Smooth Road Trip 

The itinerary starts and ends in Milan.

Road trip in Italy - a complete map with planning

Do you have more time?

If it’s your first time in Milan, you might want to treat yourself to a couple of extra days — the city deserves it. But even if you arrive early in the morning (or fly out late in the evening), you’ll still have plenty of time to wander the streets, soak up the atmosphere, and admire the stunning Duomo without rearranging your entire itinerary.

Tuscany is always wonderful. An extra day can easily be spent in historic Siena, wine tasting in Montepulciano or just sitting in a sun lounger enjoying the beautiful scenery of Val d'Orcia.

If you want to drive around Lake Garda (which takes an extra half day with stops and queues), you can add an extra day here.

Less time?

We did our road trip in Italy in 11 days during the low season in April. Then we only had 1 day in Florence, 1,5 days in Venice and 1 day in Lake Como. During the low season you can more than manage the route in that time, but keep in mind that everything takes a little longer if you travel in Italy during July/August or during holidays.


Day 1: Arrival in Milan

Collect your rental car at the airport and head to the hotel. If you have not planned to explore Milan, it is recommended that you book a hotel on the outskirts of southern Milan. In this way, you will get out of the city faster when you go to Portofino the next day.

ACCOMMODATION TIPS: The outskirts of Milan


Portofino harbour - perfect stop on a road trip in Italy
Portofino

Day 2: Portofino  

ITINERARY
Milan – Portofino (Santa Margherita) – Sestri Levante

DAILY PLANNING
Go early from Milan to Santa Margherita and park the car for a full day in one of Italy's most luxurious resorts - Portofino. You can't drive here, so take a bus or boat from Santa Margherita and enjoy the nice little town before going to Sestri Levante for a really good dinner.

ACCOMMODATION TIPS
Sestri Levante. A city that became one of our favorites on the trip!

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Portofino – The favorite village of celebrities
Sestri Levante – The stop that became memorable
Santa Margherita – the city everyone passes but few visit
Hotel Vis à Vis in Sestri Levante - Hotel review


Manarola - Cinque Terre - A perfect stop on a road trip in Italy
Cinque Terre

Day 3-4: Cinque Terre

ITINERARY
Sestri Levante – La Spezia (train/boat to Cinque Terre)

DAILY PLANNING
Today we are going to visit one of my favorite places in Italy – Cinque Terre. Cinque terre is not a place for cars, so the easiest way is to drive La Spezia and park the car. From La Spezia there are numerous boats and trains to the five villages. We took the train, which is highly recommended. Explore the area and its hiking trails and fish restaurants for two days. And you – Cinque Terre is just as pastel and beautiful as it looks in the pictures.

ACCOMMODATION TIPS
La Spezia

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Ride the train in Cinque Terre
Monterosso Al Mare – Cinque Terre's northernmost town
Vernazza – Our second stop in the Cinque Terre
Manarola - Where Cinque Terre takes my breath away
Riomaggiore – our last stop in the Cinque Terre 


San Gimignano - Tuscany - Italy road trip
San Gimignano

Day 5: Pisa

ITINERARY
La Spezia – Pisa – Volterre – San Gimignano – Radda in Chianti 

DAILY PLANNING
Today you explore Pisa and the Leaning Tower. The earlier in the morning you visit the Leaning Tower, the better. In the afternoon you go south in Tuscany and visit the beautiful small towns Voltaire and San Gimignano, before checking into a beautiful hotel in Chianti.

ACCOMMODATION TIPS
Hotel review: CDH Radda in Chianti

READ MORE
Pisa - A post about overtourism and travel disappointment
San Gimignano – towers, feuds and truffles
Lunch at Agrihotel il Palagetto
Volterra – The alabaster city on the hill


Rolling hills of Tuscany-Val-d'Orcia on a road trip in Italy
Val d'Orcia

Day 6: Tuscany

ITINERARY
Radda in Chianti – Pienza – Montepulciano – Val d'Orcia – Radda in Chianti

DAILY PLANNING
Today you drive around Tuscany's most beautiful green landscape at Val d'Orcia, but you will also have time to visit one of the towns of Pienza and Montepulciano. There are plenty of really good restaurants here, but also take the opportunity to buy the area's local truffles, wine and pecorino from one of the many delicatessens.

ACCOMMODATION TIPS
Radda in Chianti

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Pienza – Pecorino and palace in the Pope's perfect city
Val d'Orcia – Among Tuscany's most beautiful landscapes
Montepulciano – Slopes, lanes and Vino Nobile


Florence-Italy-Ponte Vechio
Florence

Day 7-8: Florence

ITINERARY
Radda in Chianti – Florence – Bologna

DAILY PLANNING
Have a delicious breakfast at the hotel's outdoor dining area before heading to Florence. In Florence, you visit the city's most famous sight - Santa Maria del Fiore - but also one of the many palaces and museums. Expect that there will be a lot of visitors in Florence all year round, so book as much as you can in advance. Stay one night in Florence to maximize your visit and watch the city wake up, before heading to Bologna the next day. 

ACCOMMODATION TIPS
Florence + Bologna (10 miles from Florence)

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Photo album from Florence
Sights in Florence - My ten favorites


The Rialto Bridge in Venice during a road trip in Italy
Venice

Day 9-10: Venice

ITINERARY
Bologna – Venice

DAILY PLANNING
Alright Venice as early in the morning as you can manage, because you'll want all the time you can get in Venice. Park the car in the large Tronchetto car park and take the water bus to your hotel. Stay centrally and preferably in one of the old palaces (even if it's expensive) – because nowhere does accommodation matter as much as in Venice.

In Venice, it's a pleasure to stroll through all the little alleyways, but don't miss taking a water taxi to the colorful islands Burano and Murano before you leave here!

ACCOMMODATION TIPS
Venice - Palazzo Madonna

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Burano - The island where the rainbow meets Venice
Venice - When the sea gets closer
Mini guide to Venice - 8 Tips before the trip
Photo album from Venice - A dream of canals and burrata


Restaurant on Lake Garda
Lake Garda

Day 11: Lake Garda

ITINERARY
Venice - Lake Garda (any location)

DAILY PLANNING
Here you can choose what you prioritize most. Either you stay in Venice as long as you can, or you head for the mountains and towards Lake Garda and explores one of the lake's small villages and restaurants. We chose to stay in Venice for the afternoon and drove straight to Peschiera del Garda for dinner. If you go earlier, you can stay in the city of romance Verona or in the wine district Valpolicella area (Veneto) on the road. 

ACCOMMODATION TIPS
Lake Garda (Lazise, ​​Riva del Garda or Peschiera del Garda)

READ MORE
The Olive Trail in Arco – A taste of Italy on the edge of the Alps
Riva del Garda – Where the mountains are reflected in Lake Garda – Italy
Discover pasta bliss at Lake Garda – On a cooking class in Italy with Stefano Rossi
Food festivals at Lake Garda – Autumn delights during Mese del Gusto


Lake Como in Italy

Day 12-13: Lake Como

ITINERARY
Lake Garda – Lake Como 

DAILY PLANNING
Take the long route around Lake Garda if you want to experience the most beautiful views of the lake (add 3-4 hours extra travel time), otherwise go directly towards Lake Como. On the way, you can stop in pretty Sirmione on the southern shore of Lake Garda and see the archaeological remains and its castle. 

Lake Como is elegant and beautiful and offers a large selection of lovely restaurants and outdoor seating. The crowning glory is the village of Bellagio at the far end of a peninsula. A perfect last stop before heading home to Sweden again. But you, by the way, shouldn't you extend the trip for a few more days here in Como before you go home? 

ACCOMMODATION TIPS
Cernobbio (budget) or Bellagio (luxury)


Day 14: Back to the airport

RESVOWN
Lake Como - Milan

DAILY PLANNING
Depending on which airport you fly from and what time of day, you can hopefully manage to take a walk by the sparkling Lake Como before you have to drive to the airport. An epic road trip is coming to an end – filled with memories of some of the world's most iconic cities and historic sites.

Ready, set, pack your bags! Now it's time to embark on your own road trip in Italy and create memories that will last a lifetime!


Do you want to read more about Italy? Here you will find more articles about cities, nature, food and hiking.

3 COMMENTS
    • Hello,
      It's great that you like the layout - we did too! :)
      Actually don't dare answer budget at the moment - car rentals, hotels and flight prices have gone up quite a bit since we went and there is a big difference between high season and low season.
      You can fly relatively cheaply to Milan if you are out in good time, you only need a small rental car in Italy and hotels are available in most price ranges. We were also 3 people who stayed in the same hotel room and traveled during the low season, so per person the trip was very affordable!

  1. Hi! Thank you for this nice site. We did a similar trip based on your blog in 15 days.

    Highlights:

    × La Spezia/Cinque Terre. Great place to stay near the station in La Spezia.

    × The small old towns in Tuscany. All are cozy and worth a visit.

    × Venice and Murano/Burano. Definitely a highlight. Stayed 2 nights here. (We parked the car in Mestre cheaply and took the train over to Venice where we were staying)

    Tips about cars. We found that we could easily find parking in most cities with a little patience. Sometimes even free parking. Avoid parking garages. There is usually always street parking and in my opinion it felt safer.

    Florence was terrible to drive in and actually one of the cities we liked the least.

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Travel blogger, gastronaut, photographer and family adventurer with over 60 countries in his luggage. Eva loves trips that include beautiful nature, hiking boots and well-cooked food. On the travel site Rucksack, she takes you to all corners of the world with the help of her inspiring pictures and texts.

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